Summary

IMPPAT Phytochemical identifier: IMPHY009898

Phytochemical name: (1R,19R)-4,5,9-Trihydroxy-4-(2-hydroxybutan-2-yl)-8-methyl-9-propan-2-yl-2,7,11-trioxa-16-azatricyclo[11.5.1.016,19]nonadec-13-ene-3,6,10-trione

Synonymous chemical names:
spiracine

External chemical identifiers:
CID:157017

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Chemical structure information

SMILES:
CCC(C1(O)C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)C(C(OC(=O)C1O)C)(O)C(C)C)(O)C

InChI:
InChI=1S/C23H35NO10/c1-6-21(5,29)23(31)17(25)18(26)33-13(4)22(30,12(2)3)19(27)32-11-14-7-9-24-10-8-15(16(14)24)34-20(23)28/h7,12-13,15-17,25,29-31H,6,8-11H2,1-5H3/t13?,15-,16-,17?,21?,22?,23?/m1/s1

InChIKey:
ZMTPMWQLYFVWSP-YHWJFGDTSA-N

DeepSMILES:
CCCCO)C=O)O[C@@H]CCN[C@@H]5C=CC5))COC=O)CCOC=O)C%17O))))C))O)CC)C)))))))))))))))O)C

Functional groups:
CC(=O)OC, CC=C(C)C, CN(C)C, CO, COC(C)=O

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
O=C1CCC(=O)OC2CCN3CC=C(COC(=O)CCO1)C23

Scaffold Graph/Node level:
OC1CCC(O)OC2CCN3CCC(COC(O)CCO1)C23

Scaffold Graph level:
CC1CCCC(C)CCC2CCC3CCC(CC(C)CC1)C23

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Phenylpropanoids and polyketides

ClassyFire Class: Macrolides and analogues

NP Classifier Biosynthetic pathway: Alkaloids

NP Classifier Superclass: Ornithine alkaloids

NP Classifier Class: Pyrrolizidine alkaloids

NP-Likeness score: 1.845

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Chemical structure download